JP2008069082A - Germicide composition and skin care preparation containing the germicide composition - Google Patents
Germicide composition and skin care preparation containing the germicide composition Download PDFInfo
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Abstract
Description
本発明は、殺菌剤組成物並びに該殺菌剤組成物を含有した皮膚外用剤に関する。 The present invention relates to a bactericidal composition and a skin external preparation containing the bactericidal composition.
従来より、手や指の除菌のためには、一般に石鹸等による洗浄が行われている。しかし、屋外等の水を使用できない場所では、手や指の洗浄ができないという問題がある。また、病院内における院内感染の防止のためには、病院従事者や来院者等の手や指の洗浄が必要であるが、石鹸等による洗浄は面倒であることから、その徹底が困難な現状がある。 Conventionally, washing with soap or the like is generally performed for sterilization of hands and fingers. However, there is a problem that hands and fingers cannot be washed in places where water cannot be used, such as outdoors. In addition, in order to prevent nosocomial infections in hospitals, it is necessary to wash hands and fingers of hospital workers and visitors. However, washing with soap etc. is cumbersome and is difficult to implement thoroughly. There is.
更には、手指の消毒や皮膚外用剤に用いられる抗菌剤は、一般に殺菌効果が強いほど、皮膚刺激性や毒性が強い。このため、手指の消毒を頻繁に行う看護師や敏感肌の人などは、手荒れや皮膚刺激による炎症などが生じ易いという問題がある。 Furthermore, antibacterial agents used for finger disinfection and skin external preparations generally have stronger skin irritation and toxicity as the bactericidal effect is stronger. For this reason, there is a problem that nurses who frequently disinfect fingers and persons with sensitive skin are likely to suffer from rough hands and inflammation due to skin irritation.
このような問題を解決するために、塩化ベンザルコニウム等の低水準消毒薬に低級アルコールを添加した外用殺菌消毒剤（特許文献１参照）、エタノールとイソプロパノールを特定量で含有した外用殺菌消毒剤（特許文献２参照）、ピロクトンオラミン、ジンクピリチオン、イソプロピルメチルフェノール等の殺菌剤の１種以上と水膨潤性粘度鉱物との複合体を含む殺菌剤組成物（特許文献３参照）などが提案されている。 In order to solve such problems, an external disinfectant containing a lower alcohol added to a low-level disinfectant such as benzalkonium chloride (see Patent Document 1), an external disinfectant containing a specific amount of ethanol and isopropanol (See Patent Document 2), and a fungicidal composition (see Patent Document 3) containing a complex of one or more fungicides such as piroctone olamine, zinc pyrithione, and isopropylmethylphenol and a water-swellable viscosity mineral are proposed. Has been.
しかし、これら殺菌剤や消毒剤により、菌の静菌作用を発揮するものの、効果的な殺菌作用までは至っていない。 However, these bactericides and disinfectants exert a bacteriostatic action, but have not yet achieved an effective bactericidal action.
また、特許文献３では、ジンクピリチオンやイソプロピルメチルフェノールが殺菌剤組成物に用いられることが開示されてはいるが、これは殺菌剤の１種と水膨潤性粘度鉱物とを複合体に形成させるものであって、ジンクピリチオンとイソプロピルメチルフェノールとを共に用いることの開示はなく、併用することにより、殺菌作用が相乗的に向上することの開示もない。 Patent Document 3 discloses that zinc pyrithione and isopropylmethylphenol are used in a fungicide composition, but this forms a complex of one type of fungicide and a water-swellable viscosity mineral. However, there is no disclosure of using both zinc pyrithione and isopropylmethylphenol, and there is no disclosure that the bactericidal action is synergistically improved by the combined use.
本発明は、前記従来技術に鑑みてなされたものであって、比較的皮膚刺激性が少なく低殺菌性の抗菌剤であるジンクピリチオンとイソプロピルメチルフェノールを用いながら、両者を併用することにより、それぞれの殺菌作用を相乗的に増強することができる殺菌剤組成物、並びに該殺菌剤組成物を含有した皮膚外用剤を提供することを課題とする。 The present invention has been made in view of the prior art, and using zinc pyrithione and isopropylmethylphenol, which are relatively low skin irritation and low bactericidal antibacterial agents, It is an object of the present invention to provide a bactericidal composition capable of synergistically enhancing the bactericidal action, and a skin external preparation containing the bactericidal composition.
すなわち、本発明は、
〔１〕 イソプロピルメチルフェノール及びジンクピリチオンとを含有してなる殺菌剤組成物、並びに
〔２〕 前記〔１〕に記載の殺菌剤組成物を含有することを特徴とする皮膚外用剤
に関する。
That is, the present invention
[1] A fungicidal composition containing isopropylmethylphenol and zinc pyrithione, and [2] a skin external preparation characterized by containing the fungicidal composition according to [1].
本発明の殺菌剤組成物は、ジンクピリチオン及びイソプロピルメチルフェノールのそれぞれの殺菌作用を相乗的に増強する。よって、高い作用を有しながら皮膚に対して低刺激性であり、安全性の高い殺菌剤組成物を得ることができる。 The bactericidal composition of the present invention synergistically enhances the bactericidal action of zinc pyrithione and isopropylmethylphenol. Therefore, it is possible to obtain a fungicidal composition having high action and low irritation to the skin and high safety.
また、本発明の皮膚外用剤は優れた殺菌作用を有するので、皮膚に塗布するだけで効果的に除菌できるうえ、殺菌剤自体の配合量を低配合量とすることができ、極めて安全性の高い皮膚外用剤を得ることができる。 Further, since the external preparation for skin of the present invention has an excellent bactericidal action, it can be effectively sterilized by simply applying it to the skin, and the blending amount of the bactericidal agent itself can be made low, which is extremely safe. Can be obtained.
本発明の殺菌剤組成物は、イソプロピルメチルフェノールとジンクピリチオンとを含有する。 The fungicidal composition of the present invention contains isopropylmethylphenol and zinc pyrithione.
イソプロピルメチルフェノールは、４−イソプロピル−３−メチルフェノールの化学構造を有し、メタクレゾールと塩化イソプロピル又はイソプロパノールとの反応により得られる。殺菌剤、防腐剤、防黴剤などとして汎用されている。 Isopropylmethylphenol has a chemical structure of 4-isopropyl-3-methylphenol and is obtained by reaction of metacresol with isopropyl chloride or isopropanol. It is widely used as a disinfectant, antiseptic, antifungal agent and the like.
ジンクピリチオンは、２−ピリジンチオール−１−オキシドの亜鉛塩であり、抗菌、ふけ防止、止痒などの作用があり、シャンプー剤などに多用されている。 Zinc pyrithione is a zinc salt of 2-pyridinethiol-1-oxide, which has antibacterial, anti-dandruff and anti-pruritic effects and is often used as a shampoo agent.
イソプロピルメチルフェノールとジンクピリチオンとの含有比は、本発明の効果を発揮すれば特に限定されないが、重量比（イソプロピルメチルフェノール：ジンクピリチオン）で１：０．１〜１：１０とするのが好ましく、１：０．２〜１：５となるように配合するのがより好ましい。ジンクピリチオンをイソプロピルメチルフェノール１重量部に対して０．１重量部未満の場合、又は１０重量部を超えて含有すると、殺菌作用の相乗的効果が期待できないために好ましくない。 The content ratio of isopropylmethylphenol and zinc pyrithione is not particularly limited as long as the effects of the present invention are exhibited, but it is preferably 1: 0.1 to 1:10 by weight ratio (isopropylmethylphenol: zinc pyrithione). : It is more preferable to mix | blend so that it may become 0.2-1: 5. When zinc pyrithione is contained in an amount of less than 0.1 part by weight or more than 10 parts by weight based on 1 part by weight of isopropylmethylphenol, a synergistic effect of bactericidal action cannot be expected.
本発明の殺菌剤組成物におけるイソプロピルメチルフェノールとジンクピリチオンとの合計の含有量は特に限定されず、殺菌剤組成物がイソプロピルメチルフェノールとジンクピリチオンのみで構成されていても良く、或いは、本発明の効果が阻害されない範囲で他の成分が含有されていても良い。他の成分としては、例えば、エタノール、イソプロピルアルコール等の溶剤の他、キレート剤、紫外線吸収剤、酸化防止剤、界面活性剤、色素、水などを例示することができる。 The total content of isopropylmethylphenol and zinc pyrithione in the fungicide composition of the present invention is not particularly limited, and the fungicide composition may be composed only of isopropylmethylphenol and zinc pyrithione, or the effects of the present invention. Other components may be contained within a range that does not impede. Examples of other components include chelating agents, ultraviolet absorbers, antioxidants, surfactants, dyes, water, and the like, in addition to solvents such as ethanol and isopropyl alcohol.
本発明の殺菌剤組成物は、皮膚外用剤などに配合して使用することができる。具体的には、創傷の消毒剤、手指消毒剤、薬用ハンドソープなどの皮膚消毒用の外用剤；ハンドクリーム、皮膚炎用ローション、制汗剤などのその他の皮膚外用剤に用いることもできる。 The disinfectant composition of the present invention can be used by blending with a skin external preparation or the like. Specifically, it can also be used for external preparations for skin disinfection such as wound disinfectants, hand disinfectants, medicinal hand soaps, and other skin external preparations such as hand creams, dermatitis lotions and antiperspirants.
本発明の殺菌剤組成物を用いて皮膚外用剤を調製する場合、本発明の効果が損なわない範囲で、化粧料や医薬品に通常用いられる成分を適宜任意に配合することができる。例えば、カルボキシビニルポリマー、アクリル酸・メタクリル酸アルキル共重合体、エチルセルロース、ヒドロキシプロピルセルロース等のゲル化剤；塩化ベンザルコニウム、トリクロサン、グルコン酸クロルヘキシジン等のその他の殺菌消毒薬；グリセリン脂肪酸エステル、ポリオキシアルキレンアルキルエーテル、ポリオキシアルキレン脂肪酸エステル等の非イオン界面活性剤；高級脂肪酸石鹸、アルキル硫酸エステル塩等の陰イオン界面活性剤；アルキルアミン塩、モノアルキル型４級アンモニウム塩等の陽イオン界面活性剤；グリシン型両性界面活性剤、アルキルアミノプロピオン酸塩等の両性界面活性剤；エタノール、イソプロパノール等の低級アルコール；１，３−ブタンジオール，グリセリン、１，２−ペンタンジオール等の多価アルコール類；オリーブ油、ツバキ油等の油脂；カルナバロウ、キャンデリラロウ等のロウ類；流動パラフィン、スクワラン等の炭化水素；メチルポリシロキサン、メチルフェニルポリシロキサン、オクタメチルシクロテトラシロキサン、デカメチルシクロペンタシロキサン等のシリコン類；ミリスチン酸イソプロピル、２−エチルヘキサン酸セチル等の脂肪酸エステル；セチルアルコール、ステアリルアルコール等の高級アルコール類；ラウリン酸、ステアリン酸、イソステアリン酸、オレイン酸等の高級脂肪酸；酸化防止剤、色素、酸・アルカリ等の添加成分、水等が挙げられる。 When preparing an external preparation for skin using the bactericidal composition of the present invention, components usually used in cosmetics and pharmaceuticals can be optionally arbitrarily blended within the range in which the effects of the present invention are not impaired. For example, carboxyvinyl polymer, acrylic acid / alkyl methacrylate copolymer, gelling agent such as ethyl cellulose, hydroxypropyl cellulose; other bactericidal disinfectants such as benzalkonium chloride, triclosan, chlorhexidine gluconate; glycerin fatty acid ester, poly Nonionic surfactants such as oxyalkylene alkyl ethers and polyoxyalkylene fatty acid esters; Anionic surfactants such as higher fatty acid soaps and alkyl sulfate esters; Cationic interfaces such as alkylamine salts and monoalkyl quaternary ammonium salts Activators; amphoteric surfactants such as glycine-type amphoteric surfactants and alkylaminopropionates; lower alcohols such as ethanol and isopropanol; 1,3-butanediol, glycerin, 1,2-pentanediol, etc. Oils and fats such as olive oil and camellia oil; waxes such as carnauba wax and candelilla wax; hydrocarbons such as liquid paraffin and squalane; methylpolysiloxane, methylphenylpolysiloxane, octamethylcyclotetrasiloxane, decamethylcyclopenta Silicones such as siloxane; Fatty acid esters such as isopropyl myristate and cetyl 2-ethylhexanoate; Higher alcohols such as cetyl alcohol and stearyl alcohol; Higher fatty acids such as lauric acid, stearic acid, isostearic acid and oleic acid; Antioxidation Agents, dyes, additives such as acids and alkalis, water and the like.
皮膚外用剤を調製する場合、本発明の殺菌剤組成物の配合量は特に限定されないが、十分な殺菌効果を発揮させる観点から、皮膚外用剤中、０．０１重量％以上が好ましく、より好ましくは０．１重量％以上である。また、皮膚刺激を抑制する観点から、５重量％以下が好ましく、より好ましくは２重量％以下である。これらから、殺菌剤組成物の配合量は、皮膚外用剤中、０．０１〜５重量％が好ましく、０．１〜２重量％がより好ましい。 When preparing a skin external preparation, the blending amount of the bactericidal composition of the present invention is not particularly limited, but from the viewpoint of exerting a sufficient bactericidal effect, 0.01% by weight or more is preferable, and more preferable. Is 0.1% by weight or more. Further, from the viewpoint of suppressing skin irritation, it is preferably 5% by weight or less, more preferably 2% by weight or less. From these, 0.01-5 weight% is preferable in a skin external preparation, and, as for the compounding quantity of a disinfectant composition, 0.1-2 weight% is more preferable.
実施例１
（供試菌）
供試菌として、Pseudomonas aeruginosa IFO13275（緑膿菌）およびCandida albicans IFO1594（酵母）を用いた。
Example 1
(Test bacteria)
Pseudomonas aeruginosa IFO13275 (Pseudomonas aeruginosa) and Candida albicans IFO1594 (yeast) were used as test bacteria.
（接種用菌液の調製）
接種用菌液としては、緑膿菌の場合、寒天培地で３５℃で培養後、更にブイヨン培地に移植して３５℃で培養した。得られた培養液をブイヨン培地で約１０８個／ｍｌに希釈したものを接種用菌液とした。
(Preparation of bacterial solution for inoculation)
In the case of Pseudomonas aeruginosa, the bacterial solution for inoculation was cultured at 35 ° C. on an agar medium, then transplanted to a bouillon medium and cultured at 35 ° C. A solution obtained by diluting the obtained culture solution to about 10 8 cells / ml with a bouillon medium was used as a bacterial solution for inoculation.
また、酵母の場合は、寒天培地で３０℃で培養後、更にブイヨン培地に移植して３０℃で培養し、得られた培養液をブイヨン培地で約１０７個／ｍｌに希釈したものを接種用菌液とした。 In the case of yeast, after culturing on an agar medium at 30 ° C., transplanted to a bouillon medium and cultivating at 30 ° C., and inoculating the obtained culture solution diluted to about 10 7 cells / ml with bouillon medium. The bacterial solution was used.
（被験物質の希釈系列の調製）
ジンクピリチオン、イソプロピルメチルフェノール（以下、ＩＰＭＰと略す。）およびジンクピリチオンとＩＰＭＰの等重量混合物をＤＭＳＯにて５０００μｇ／ｍＬの濃度に溶解した液を調製した。この液を倍倍希釈し、５０００、２５００、１２５０、６２５、３１３、１５６、７８、３９、２０、１０μｇ／ｍＬの各濃度の希釈系列を得た。
(Preparation of dilution series of test substance)
A solution in which zinc pyrithione, isopropylmethylphenol (hereinafter abbreviated as IPMP) and an equal weight mixture of zinc pyrithione and IPMP were dissolved in DMSO to a concentration of 5000 μg / mL was prepared. This solution was diluted twice to obtain a dilution series having respective concentrations of 5000, 2500, 1250, 625, 313, 156, 78, 39, 20, and 10 μg / mL.
（最小殺菌濃度（ＭＢＣ）の測定）
恒温槽で６０℃に保温した寒天培地９．７５ｍＬに、上記被験物質を含む希釈系列の液０．２５ｍＬづつを加え、十分に混和後、φ６０ｍｍのシャーレに流し込み、平板に固めた。
(Measurement of minimum bactericidal concentration (MBC))
To 9.75 mL of the agar medium kept at 60 ° C. in a thermostatic bath, 0.25 mL of the dilution series solution containing the test substance was added, mixed thoroughly, poured into a petri dish of φ60 mm, and solidified on a flat plate.
緑膿菌の場合、寒天培地にＨＩ寒天培地を用い、上記接種用菌液を約１ｃｍの長さに画線した。培養は３５℃で行い、５日後の菌の生育の有無を判定した。また、酵母の場合は、寒天培地にポテトデキストロース寒天培地を用い、上記接種用菌液を約１ｃｍの長さに画線した。培養は２５℃で行い、５日後の菌の生育の有無を判定した。 In the case of Pseudomonas aeruginosa, an HI agar medium was used as the agar medium, and the above bacterial solution for inoculation was streaked to a length of about 1 cm. Culturing was performed at 35 ° C., and the presence or absence of bacterial growth after 5 days was determined. In the case of yeast, a potato dextrose agar medium was used as the agar medium, and the inoculum was streaked to a length of about 1 cm. Culturing was performed at 25 ° C., and the presence or absence of bacterial growth after 5 days was determined.
５日間培養後、生育の認められなかった寒天平板の画線中央部分を、火炎滅菌したミクロスパーテルで６ｍｍ画の正方形にくりぬき、これをブイヨン培地にて培養した。尚、緑膿菌の場合、ブイヨン培地にＳＣＤブイヨン培地を用い、３５℃で３日間培養した。また、酵母の場合、ブイヨン培地にＧＰブイヨン培地を用い、２５℃で３日間培養した。このときに生育の認められなかった最小濃度をＭＢＣとして求めた。結果を表１に記す。 After culturing for 5 days, the central portion of the agar plate where no growth was observed was cut into a 6 mm square with a flame-sterilized microspatel, and this was cultured in a bouillon medium. In the case of Pseudomonas aeruginosa, an SCD bouillon medium was used as a bouillon medium and cultured at 35 ° C. for 3 days. In the case of yeast, a GP broth medium was used as a broth medium and cultured at 25 ° C. for 3 days. At this time, the minimum concentration at which no growth was observed was determined as MBC. The results are shown in Table 1.
表１の結果から、ジンクピリチオン又はＩＰＭＰ単独では、緑膿菌に対して殺菌作用を奏しないが、ジンクピリチオンとＩＰＭＰを併用して用いると、緑膿菌に対して優れた殺菌作用を奏することが分かる。 From the results in Table 1, it can be seen that zinc pyrithione or IPMP alone does not have a bactericidal action against Pseudomonas aeruginosa, but when zinc pyrithione and IPMP are used in combination, it has an excellent bactericidal action against Pseudomonas aeruginosa. .
また、ジンクピリチオン単独では酵母に対して殺菌作用を奏しないが、ＩＰＭＰは単独で３１３μｇ／ｍＬの濃度で殺菌作用を発揮する。一方、ジンクピリチオンとＩＰＭＰとを併用して用いると、ＩＰＭＰの使用量を半減させたとしても、ＩＰＭＰ単独の場合と同等の殺菌作用を発揮することが分かる。 In addition, zinc pyrithione alone does not exert a bactericidal action against yeast, but IPMP alone exerts a bactericidal action at a concentration of 313 μg / mL. On the other hand, when zinc pyrithione and IPMP are used in combination, even if the amount of IPMP used is halved, it can be seen that the same bactericidal action as that of IPMP alone is exhibited.
よって、ジンクピリチオンとＩＰＭＰを併用すると、それぞれが有する殺菌効果を相乗的に増強していることが分かる。 Thus, it can be seen that the combined use of zinc pyrithione and IPMP synergistically enhances the bactericidal effect of each.
以下、本発明に係る殺菌剤組成物を配合した皮膚外用剤の配合例を示す。尚、配合量は重量％である。 Hereafter, the example of a skin external preparation which mix | blended the disinfectant composition which concerns on this invention is shown. In addition, a compounding quantity is weight%.
（処方例１：手指消毒剤）
ジンクピリチオン ０．２
イソプロピルメチルフェノール ０．１
アクリル酸・メタクリル酸アルキル共重合体 ０．１
カルボキシビニルポリマー ０．３
２−アミノ−２−メチル−１−プロパノール ０．２５
ドデカメチルシクロヘキサシロキサン ０．１
エタノール ７０．０
精製水 残 分
合 計 １００．０
(Prescription Example 1: Hand sanitizer)
Zinc pyrithione 0.2
Isopropylmethylphenol 0.1
Acrylic acid / alkyl methacrylate copolymer 0.1
Carboxyvinyl polymer 0.3
2-Amino-2-methyl-1-propanol 0.25
Dodecamethylcyclohexasiloxane 0.1
Ethanol 70.0
Purified water residue Total 100.0
（処方例２：薬用ハンドソープ）
ラウリン酸 １０．０
ミリスチン酸 ３．０
パルミチン酸 １．０
オレイン酸 １．０
水酸化カリウム ５．０
ヤシ油脂肪酸ジエタノールアミド ４．０
ジンクピリチオン ０．２
イソプロピルメチルフェノール ０．２
香料 ０．２
精製水 残 分
合 計 １００．０
(Prescription Example 2: Medicinal Hand Soap)
Lauric acid 10.0
Myristic acid 3.0
Palmitic acid 1.0
Oleic acid 1.0
Potassium hydroxide 5.0
Palm oil fatty acid diethanolamide 4.0
Zinc pyrithione 0.2
Isopropylmethylphenol 0.2
Fragrance 0.2
Purified water residue Total 100.0
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
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| JP2006246994A JP5013790B2 (en) | 2006-09-12 | 2006-09-12 | Disinfectant composition and skin external preparation containing the disinfectant composition |
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| Application Number | Priority Date | Filing Date | Title |
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| JP2006246994A JP5013790B2 (en) | 2006-09-12 | 2006-09-12 | Disinfectant composition and skin external preparation containing the disinfectant composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2008069082A true JP2008069082A (en) | 2008-03-27 |
| JP5013790B2 JP5013790B2 (en) | 2012-08-29 |
Family
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Country Status (1)
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| JP (1) | JP5013790B2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010112578A1 (en) * | 2009-04-03 | 2010-10-07 | Glaxo Group Limited | 4 -isopropyl-3-methylphenol for the treatment of inflammation |
| WO2010112577A1 (en) * | 2009-04-03 | 2010-10-07 | Glaxo Group Limited | Antibacterial composition comprising 4 -isopropyl-3-methylpheno and zinc ions |
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| JP2006045126A (en) * | 2004-08-05 | 2006-02-16 | Lion Corp | Composition for preventing dandruff and itching |
| JP2007126778A (en) * | 2005-11-02 | 2007-05-24 | Osaka Kasei Kk | Antibacterial-imparting processing solution for fiber |
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| JPH07157415A (en) * | 1993-12-03 | 1995-06-20 | Shiseido Co Ltd | Hair cosmetic |
| JPH0873325A (en) * | 1994-09-06 | 1996-03-19 | Kao Corp | Hair-tonic and hair-growing agent |
| JPH08277371A (en) * | 1995-02-09 | 1996-10-22 | Kanebo Kasei Kk | Antimicrobial and antifungal coating composition |
| JPH10265408A (en) * | 1997-03-25 | 1998-10-06 | Lion Corp | Sterilizer composition |
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| JPH11269043A (en) * | 1998-03-23 | 1999-10-05 | Shiseido Co Ltd | Cosmetic for scalp and hair |
| JP2001172159A (en) * | 1999-12-20 | 2001-06-26 | Lion Corp | Low irritative antibacterial cosmetic |
| JP2005206538A (en) * | 2004-01-23 | 2005-08-04 | Kao Corp | Cosmetic for scalp and hair |
| JP2006045126A (en) * | 2004-08-05 | 2006-02-16 | Lion Corp | Composition for preventing dandruff and itching |
| JP2007126778A (en) * | 2005-11-02 | 2007-05-24 | Osaka Kasei Kk | Antibacterial-imparting processing solution for fiber |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010112578A1 (en) * | 2009-04-03 | 2010-10-07 | Glaxo Group Limited | 4 -isopropyl-3-methylphenol for the treatment of inflammation |
| WO2010112577A1 (en) * | 2009-04-03 | 2010-10-07 | Glaxo Group Limited | Antibacterial composition comprising 4 -isopropyl-3-methylpheno and zinc ions |
| CN102378627A (en) * | 2009-04-03 | 2012-03-14 | 葛兰素集团有限公司 | Antibacterial composition comprising 4 -isopropyl-3-methylpheno and zinc ions |
| JP2012522752A (en) * | 2009-04-03 | 2012-09-27 | グラクソ グループ リミテッド | Antibacterial composition comprising 4-isopropyl-3-methylphenol and zinc ions |
| CN102378627B (en) * | 2009-04-03 | 2013-10-30 | 葛兰素集团有限公司 | Antibacterial composition comprising 4 -isopropyl-3-methylpheno and zinc ions |
| RU2535010C2 (en) * | 2009-04-03 | 2014-12-10 | Глаксо Груп Лимитед | Antibacterial composition, containing 4-isopropyl-3-methylphenol and zinc ions |
| AU2010230196B2 (en) * | 2009-04-03 | 2015-04-02 | Glaxo Group Limited | Antibacterial composition comprising 4 -isopropyl-3-methylpheno and zinc ions |
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|---|---|
| JP5013790B2 (en) | 2012-08-29 |
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